6-Fluoro-1-indanone → 2,3-Dihydro-6-fluoro-1H-inden-1-ol

HRID 237265Notes

Reaction equation

HRID 237265 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>ClCCCl.CO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 15194646-Fluoro-1-indanoneHCID 4311764Sodium borohydride

Product 1

HCID 613834992,3-Dihydro-6-fluoro-1H-inden-1-olYield 97.6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

To a solution of 6-fluoro-indan-1-one (0.50 g, 3.3 mmol) in DCE (10 mL) and MeOH (10 mL) was added NaBH4 (0.25 g, 6.6 mmol). After 30 min the reaction was quenched with H2O (10 mL) and extracted with CH2Cl2 (3×20 mL). The organic layers were combined and dried to give the title compound (0.49 g, 97%). MS (ESI): mass calcd. for C9H7FO, 150.1; m/z found, 151.4 [M+H]+. 1H NMR (CDCl3): 7.23-7.13 (m, 1H), 7.09 (dd, J=8.6, 2.5 Hz, 1H), 6.99-6.90 (m, 1H), 5.21 (t, J=6.3 Hz, 1H), 3.13-2.91 (m, 1H), 2.85-2.68 (m, 1H), 2.63-2.44 (m, 1H), 2.09-1.74 (m, 2H).

Workup

  1. customAfter 30 min the reaction was quenched with H2O (10 mL)
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. customdried

Sources & evidence

ORD record
ord-644ed4a1df314c70b61439dc48c28ab4
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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